5 Places to Grab a Really Good Cocktail

coup glass holds a cocktail with orange liquer and foamy top at waypoint bar at the grove in bend oregon

Are you due for a friends’ night out? Craving some of Bend’s best cocktails? We’ve listed just a few of the best bars in Bend to meet up for anything from champagne margaritas to cigars and pizza. Enjoy a Central Oregon evening of happy hour, pregame, or a nightcap with a few of the best cocktails in Bend!

1. San Simón

Set in Tin Pan Alley downtown, this gem of a bar offers indoor and outdoor seating, fantastic cocktails, and build-your-own charcuterie boards. Dubbed the “Cheers” bar for cocktails, San Simón is a place for all types of meet-ups. (During the summer, we love their boozy slushie cocktails.)

Start your evening out with a glass of wine before dinner, gather for classic daiquiris and charcuterie boards, or come for a nightcap of painkillers affront the fire pit. Note: a painkiller is a cocktail of orange juice, coconut creme, pineapple, rum, and nutmeg that originated in the British Virgin Islands and is popular in New Orleans.

When you’re hungry, ask for a charcuterie menu that allows you to choose your own meats, cheeses, pickles, and conservas. Don’t forget to add a chocolate bar from local chocolate maker Fawkes Confectionery. Add this to your list of the best bars in Bend!

hand holds a bright yellow colored cocktail in front of a brick wall at san simon bar in bend oregon
Copyright Eat Drink Media

San Simón is open daily from 2 pm ’til late.
845 Tin Pan Alley, Bend

2. Waypoint BBC

When you don’t want to venture downtown, head to Waypoint BBC at The Grove Market Hall. It’s the second taproom from Bend Brewing Company and features BBC beers, specialty cocktails, a curated wine list, and their own label of spirits. There’s plenty of indoor and outdoor seating and a large fireplace to gather around.

Tuesday is local’s night for beer, wine, and cocktail specials. Check out their social media page for updates on live music, which takes place on their spacious outdoor patio. Waypoint doesn’t offer food, but you can order from surrounding food carts and counters inside of The Grove. Try delicious egg rolls and fried wontons from ThAiPAS, fast-casual Italian from Sunny’s Carrello, and lobster rolls from Sebastian’s Seafood.

Waypoint is open Wednesday through Saturday from noon ’til close;
Sunday through Tuesday from 3 pm ’til close.
921 NW Mt. Washington Drive, Bend

3. The Dogwood Cocktail Cabin

Dogwood is often voted one of the the best bars in Bend, and for good reason. They have an impressive cocktail list while offering delicious bites that you won’t believe come from a bar kitchen. And, when you’re in the mood for that young and free feeling, head to Dogwood on a weekend evening. You might just catch a DJ playing throwback and earworms. 

The cocktail menu features plenty of aromatics, herbs, and infusions. Think rosebuds, CBD, specialty bitters, and orange blossom. And it doesn’t end there — opt for low ABV cocktails or even a curated mocktail in lieu of imbibing.

The cabin-like bar offers plenty of seating options, including a dart room, outdoor tables, and cozy nooks. Stop by between 5 and 7 PM or anytime during open hours on Sunday for Cabin Fever, aka happy hour. Select eats and drinks are 25% off.

Fancy cocktail glass holds an orange cocktail garnished with an orange peel at Dogwood cocktail bar in bend oregon
Copyright Eat Drink Media

Dogwood is open Tuesday through Sunday from 5 pm ’til midnight.
147 NW Minnesota Avenue, Bend

4. Velvet

From the outside, Velvet looks like a small plant shop. (You might even notice the sign explicitly stating that it’s anything but.) Step inside and you’ll find intimate seating, plenty of plant babies, and two bars—both upstairs and downstairs. 

The drinks are generous in size, beautifully garnished, and unique. Like their champagne jalapeño margarita, an enticing blend of silver tequila, jalapeño, cucumber, housemade lemonade, and sparkling wine. Or, try a blue velvet made with house-infused blueberry vodka, homemade lemonade, Yerba Maté, and infused Oregon blueberries.

Pre-game your evening plans with a slice from Pizza Mondo next door, or order bacon-wrapped apricot skewers and BLT sliders from Velvet. The bar also serves up Aussie meat pies and a few hot drinks that are perfect for sweater weather.

Hand holds a couple glass filled with a martini and skewer of olives at Velvet bar in Bend Oregon
Courtesy The Bend House

Velvet is open daily from 5 pm ’til midnight.
805 NW Wall Street, Bend

5. O’Kanes at McMenamins Old St. Francis School

O’Kane’s is one piece of the larger McMenamins Old St. Francis School complex. The 1936 Catholic schoolhouse was transformed into a hotel in 2004 and has been outfitted with a pub, brewery, movie theater, and beautiful soaking pool. 

Set in the schoolhouse’s former garage, O’Kanes offers patrons Northwest-style pub fare, handcrafted beverages, and cigar smoking. You can sit inside and curl up in front of the 1896 Round Oak stove or enjoy the wood-burning fire pits on the patio. Find their patio situated between hotel guestrooms and the soaking pool. You’ll see guests walking through the patio in bathrobes to get to the pool and wonder why you’re not doing the same.

The cocktail menu at O’Kane’s features bourbons and whiskeys from around the globe. Pick your poison, grab a cigar, and don’t forget a growler fill of beer on your way out. Catch happy hour specials from 3 to 6 pm every Sunday through Thursday.

Large brick building with snow on the ground, lit up at night with sign that reads McMenamins Pub and Brewery in Bend Oregon
Courtesy McMenamins Old St. Francis School

O’Kanes is open weekdays from 3 pm ’til close;
weekends noon ’til close.
700 NW Bond Street, Bend

Could these be some of the best bars in Bend? We’ll let you decide! Tag @eatdrinkbend when you visit one or more of these cocktail bars!

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About Eat Drink Bend

Nancy Patterson of Eat Drink Bend takes a picture of beer on a table outside in Bend, Oregon.

I wanted to share more than where to eat, but what to eat. And not just what, but why? From where is the food resourced? Should it be paired with a beer, or a cocktail—and what kind? But most importantly, share the faces and tell the stories behind the people who make it all happen, showing support for small business in and around Bend.

– Nancy Patterson, Founder